Shelter Island Vacation Rentals

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About Shelter Island

If you’re looking for a Hamptons-esque getaway but want to escape the busy crowds, our Shelter Island vacation rentals are calling. This small community exudes tranquility amongst the more populated areas surrounding it, earning Shelter Island the nickname the “not-Hamptons” among locals.

Where is Shelter Island, NY?

Shelter Island is tucked on the eastern end of Long Island, just north of New Haven. This special place is a five-minute ferry ride from the ritz of the Hamptons, and a three-hour drive from New York City, but feels totally separate—in fact, Shelter Island is only accessible by ferry. The population of 2,400 expands to five times that during the summers, but the area still retains its charm. With four marinas, public beaches, and plentiful water access, our Shelter Island beach houses afford a getaway for you to truly unwind and relax.

Things to do near Shelter Island, NY

Shelter Island is a recreation destination, and visitors from all walks of life will find an outdoor activity they can enjoy. Start your day with a trip to Marie Eiffel Market to grab a picnic lunch, before renting bicycles to cruise along the streets. Book a group kayak tour—or simply rent one for your own personal excursion—to explore the warm waters of the bay. The nearby Mashomack Preserve is perfect for a morning run or evening sunset stroll, with more than 2,000 acres of beautiful creeks, woodlands, and coastline. Shelter Island also offers golf courses, tennis courses, and sailing excursions so you’ll never be short on activities.

No trip to Shelter Island would be complete without a visit to Sylvester Manor. What was once a 19th-century plantation has been upgraded to an organic farm with cultural events, farm visits, and educational programs. Stop by their farmstand for fresh produce, or on Saturday mornings you can head to the farmers market at Havens House Museum for baked goods, produce, cheeses, and pickles. Be sure to stock up on local goodies to whip up something tasty in a fully-equipped kitchen of our Shelter Island vacation rentals! In the evenings, stop by Sunset Beach Restaurant for oysters, or grab some fresh-scooped ice cream from Tuck Shop, before checking out a concert at the Perlman Music Program.

Shelter Island is the perfect place for a quiet getaway. Families and couples alike return year after year to experience this one-of-a-kind town. Browse our Shelter Island vacation rentals today to book your own peaceful slice of the “not-Hamptons.”